Chemical Constituents of Plants from the Genus Dracocephalum

REVIEW

Chemical Constituents of Plants from the Genus Dracocephalum

by Qi Zeng^a), Hui-Zi Jin*^a), Jiang-Jiang Qin^a), Jian-Jun Fu^a), Xiao-Jia Hu^a), Jian-Hua Liu^a), Lan Yan^a), Ming Chen^a), and Wei-Dong Zhang*^a)^b)
^a) Department of Chemistry and Bioactivity of Traditional Chinese Medicine, School of Pharmacy,
Shanghai Jiao Tong University, 800 DongChuan Road, 200240, Shanghai, P. R. China
^b) Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, 325 GuoHe Road, 200433 Shanghai, P. R. China
(phone/fax: þ 86-21-34205989; e-mail: [e-mail]; [e-mail])


Contents

1. 
   Introduction
   
2. 
   Chemical Constituents
   
   1. 
      Terpenoids
      
      1. 
         Triterpenoids
         
      2. 
         Steroids
         
      3. 
         Diterpenoids
         
      4. 
         Sesquiterpenes
         
      5. 
         Monoterpenoids
         
   2. 
      Flavonoids
      
   3. 
      Alkaloids
      
   4. 
      Lignans
      
   5. 
      Phenols
      
   6. 
      Coumarins
      
   7. 
      Cyanogenic Glucosides
      
   8. 
      Others
      
3. 
   Biological Activities
   
   1. 
      Antioxidant Activity
      
   2. 
      Antihypoxic Activity
      
   3. 
      Immunomodulatory Activity
      
   4. 
      Antitumor Activity
      
   5. 
      Antimicrobial Activity
      
   6. 
      Trypanocidal Activity
      
   7. 
      Cardiovascular Protective Effects
      
   8. 
      Others
      
4. 
   Concluding Remarks
   

1. 
   Introduction. – Dracocephalum is a genus of ca. 60 species of flowering plants in the family Lamiaceae, native to temperate regions of the Northern Hemisphere. In this genus, 32 species and seven varieties are distributed in northeast, northwest, north, and
   

2010 Verlag Helvetica Chimica Acta AG, Z rich
southwest of China [1]. Among them, D. moldavica is used as folk medicine for coronary heart disease and hypertension [2]. The aerial part of D. heterophyllum is a traditional medicine for asthma and gastropathy in Xinjiang and Tibet [ 3][4]. In Tibet, the native people use the herbal D. tanguticum to treat chronic bronchitis, hepatitis, and gastritis [5]. Recently, much attention has been paid to Dracocephalum genus and its chemical constituents because of their diverse activities, such as antioxidant, antihypoxic, and immunomodulatory activities, etc. In this review, we summarize the phytochemical progress and list the compounds reported from the genus Dracocepha- lum over the past decades. The biological activities of this genus are also covered at the end of this review.

2. 
   Chemical Constituents. – Since the 1970s, compounds 1 – 246, including ter- penoids, steroids, flavonoids, alkaloids, lignans, phenols, coumarins, and cyanogenic glucosides, have been identified from the genus Dracocephalum, and most of the compounds were isolated from the whole plants of this genus [6 – 46]. Their structures are shown below, and their names and the corresponding plant sources are collected in the Table. As can be seen, terpenoids are the dominant constituents within the genus Dracocephalum.
   
   1. 
      Terpenoids. 2.1.1. Triterpenoids. Twenty-two triterpenoids, 1 – 22, were isolated from the genus Dracocephalum [6 – 16]. Oleanane-type triterpenoids, 1 – 4, were isolated from various Dracocephalum species, such as D. tanguticum, D. moldavica, D. kotschyi, and D. forrestii. Ursane-type triterpenoids, 5 – 18, and lupane-type triterpe- noids, 19 – 22, were also isolated from the genus Dracocephalum.
      
      2.